We tried this at Daltic and I know Standard Treasury (YC) tried this as well.
Buying a small bank with a healthy federal charter is definitely the way to go over trying to start a new charter (FDIC hasn't given out a new charter in years and even if they do, de novo status is very cumbersome). The real challenge is getting around the Bank Holding Company Act with respect to raising capital. Basically, if any entity has a significant stake in a US bank (5-10% can trigger this) they are subject to BHCA which includes scrutiny from federal regulators (Plural!) over your books and a legal duty to bail the bank out. Our idea around this, consulting with a top financial attorney and consulting firm, was to get a consortium of wealthy individuals who would not exceed the limits individually and wouldn't be "acting in concert" with each other (which also triggers BHCA).
But even after this, any major shift in the bank's operations, including a re-architecture of technology is subject to regulatory oversight, similar to de novo status. Also, not to mention background checks from not only the FBI but also the CIA. Replacing management (which you probably want to do) is also a major change in bank operations. You also need a CEO who the regulators approve, and has previous CEO-level experience at another charter. We also had someone like this lined up.
We got pretty far in this process, but decided to put our efforts elsewhere. Seems ST did as well. Curious if you've found the same things, happy to chat further about what we learned (email in profile).
Edit: Of course, all the fun begins once you successfully acquire a charter. The real business in acquiring a bank is not to make money on loans. It turns out, despite the monopolistic access to cheap capital from depositors, non-bank lenders do a much better job at making high margin risk-adjusted loans (see https://foundationcapital.com/fcideasfintech). I believe the real opportunity for a tech-first bank is to be a whole sale and commercial bank, and tackle the $300B+ treasury services industry.
They make a mechanism for certain types of users to create accounts -- lets say only those with a valid HN account with a karma and age of over X + Y
I create the account and get the account and routing number
I then use this to direct deposit some portion of my pay into this account.
I have no access to the account aside through their meta app.
I give full autonomy to their bank and app to the funds in that account -- and I only get reports on usage and spend through the app - and I gate keep all transactions with a yay/nay -- but I never have access to the account itself in the chartered bank.
Instead, I just must commit to depositing say $1K per month in the account.
In the app - I can then only sign up for transaction types or vendors that fit within that particular deposit level.
They don't raise money for the bank at all.
They raise money for the app only.
(needs tweaking -- but the seed of what I mean is there)
unfortunately there are regs about chartered banks doing non-banking activities ... we'll talk more over the weekend, but I can give you way more details
